WO1988008696A1 - Utilisation de derives de 2,6-dinitro-aniline dans des teintures pour cheveux et nouveaux derives de 2,6-dinitro-aniline - Google Patents

Utilisation de derives de 2,6-dinitro-aniline dans des teintures pour cheveux et nouveaux derives de 2,6-dinitro-aniline Download PDF

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Publication number
WO1988008696A1
WO1988008696A1 PCT/EP1988/000260 EP8800260W WO8808696A1 WO 1988008696 A1 WO1988008696 A1 WO 1988008696A1 EP 8800260 W EP8800260 W EP 8800260W WO 8808696 A1 WO8808696 A1 WO 8808696A1
Authority
WO
WIPO (PCT)
Prior art keywords
aniline
dinitro
hydroxyethyl
amino
hair
Prior art date
Application number
PCT/EP1988/000260
Other languages
German (de)
English (en)
Inventor
Thomas Clausen
Eugen Konrad
Original Assignee
Wella Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wella Aktiengesellschaft filed Critical Wella Aktiengesellschaft
Priority to BR888807040A priority Critical patent/BR8807040A/pt
Publication of WO1988008696A1 publication Critical patent/WO1988008696A1/fr
Priority to DK716588A priority patent/DK716588A/da
Priority to FI890005A priority patent/FI890005A/fi
Priority to NO89890020A priority patent/NO890020L/no

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the invention relates to the use of nitro dyes for dyeing hair, certain 2,6-dinitro-aniline derivatives being used as nitro dyes, as well as agents containing 2,6-dinitro-aniline derivatives and new 2,6-dinitro-aniline derivatives.
  • nitro dyes are widely used in hair dyes. They are used in oxidation hair dyes as additives for the creation of natural or fashionable shades. By combining several differently colored nitro dyes, it is also possible to produce hair dyes that can dye hair in natural to fashionable shades without the use of oxidizing agents.
  • the combination of an orange dyeing and a blue-dyeing nitro dye can produce natural-looking brown dyeings.
  • nitro dyes must be toxicologically and dermatologically be harmless. Their use in oxidation hair dyes presupposes that they are stable in the presence of hydrogen peroxide in an alkaline solution. In addition, good light, acid and rub fastness is required for the hair colorations produced. Finally, it should be possible to produce the nitro compounds using the simplest possible methods.
  • R is H, C 1 -C 4 alkyl, C 2 -C 4 monohydroxyalkyl or C 3 -C 4 dihydroxyalkyl and X is one of the
  • the color scale can be used up to the value of the compounds of the general formula (I) Extend the red area. This makes it possible, by combining these dyes with suitable blue or violet dyes, not only to produce natural-looking brown colorations, but also to produce fashionable, reddish hair colors without the additional use of red dyes.
  • 2,6-dinitro-aniline derivatives of the general formula (I) is for coloring and physiological reasons, where R is 2-hydroxyethyl or 2,3-dihydroxy-propyl and X represents one of the radicals CH 3 , CF 3 , CH 2 OH, OCH 3 , OCH 2 CH 2 OH, OCH 2 CH (OH) CH 2 OH, Cl or Br, preferred as a dye in hair dyes.
  • the compounds of the general formula (I) are very suitable yellow to red-orange nitro dyes for coloring human hair. They are readily soluble in water and have excellent storage stability.
  • the present application therefore also relates to an agent for dyeing hair with a dye and cosmetic additives customary for hair dye, characterized in that it is a 2, 6-dinitro-aniline derivative of the general formula (I), preferably in an amount of 0, 01 to 2.0 percent by weight.
  • an agent for dyeing hair with a dye and cosmetic additives customary for hair dye characterized in that it is a 2, 6-dinitro-aniline derivative of the general formula (I), preferably in an amount of 0, 01 to 2.0 percent by weight.
  • preference is given to those which contain a 2,6-dinitro-aniline derivative of the formula (I) in which R is 2-hydroxyethyl or 2,3-dihydroxypropyl and X has the meaning given in the formula (I).
  • the hair dye composition according to the invention relates both to an embodiment in which it is used without the addition of an oxidizing agent and to a further embodiment in which the addition of an oxidizing agent is required.
  • the former hair dye without the addition of an oxidizing agent is an agent which, in addition to the dyes of the formula (I) indicated, can also contain other known dyes which are absorbed directly onto the hair.
  • these dyes known for hair coloring the following may be mentioned, for example: Aromatic nitro dyes, such as, for example, 2-amino-4-nitro-phenol, picramic acid, 1- (2'-hydroxy ethyl) amino-2-amino-4-nitrobenzene, 4- (2'-ureidoethyl) amino-nitrobenzene, 4- (2, 3'-dihydroxypropyl) amino-3-nitro-trifluoromethylbenzene, 4- (2 ' -Hydroxyethyl) amino-3-nitro-toluene, 1,4-bis (2'-hydroxyethyl) amino-4-N-ethyl-2-nitro-benzene, 2-nitro-4- (2'-hydroxyethyl) amino- aniline, 4-bis (2'-hydroxyethyl) amino-1-
  • the preparation form of the hair dye described here can be, for example, a solution, in particular an aqueous or aqueous-alcoholic solution.
  • Preferred forms of preparation are also a cream, a gel or an emulsion, and they can also be sprayed in a mixture with a propellant gas or by means of a pump.
  • the dyes of the general formula (I) should be present in this hair dye without the addition of oxidizing agents in a concentration of about 0.01 to 2.0 weight percent, preferably from 0.01 to 1.0 percent by weight.
  • the total content of the dyes which are applied directly to the hair is in the range of about 0.01 to 3.0 percent by weight.
  • the pH of this colorant is in the range from 3 to 10.5, in particular at pH 7.5 to 9.5, the desired alkaline pH being set primarily with ammonia, but also with organic amines such as, for example Monoethanolamine or triethanolamine can be made.
  • the hair colorant described above without the addition of an oxidizing agent can of course also contain cosmetic polymers, as a result of which the hair is set at the same time as the coloring.
  • Such agents are generally referred to as tinting or color strengthening agents.
  • polymers known for this purpose in cosmetics are, for example, polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol or polyacrylic compounds such as acrylic or methacrylic acid polymers, basic polymers of esters from these two acids and amino alcohols or the salts or quaternization products thereof, polyacrylonitrile, polyvinyl lactams and copolymers of compounds such as, for example, polyvinyl pyrrolidone-vinyl acetate and the like are mentioned.
  • Natural polymers such as chitosan centacety lated chitin) or chitosander derivatives, can also be used for the purpose mentioned.
  • the polymers are contained in this agent in the amount of about 1 to 5 percent by weight customary for such agents.
  • the pH of the agent is in the range of about 6.0 to 9.0.
  • This hair dye with additional setting is used in a known and customary manner by moistening the hair with the setting agent, setting (inserting) the hair for the hairstyle and subsequent drying.
  • the hair dye described above may optionally contain further additives customary for hair coloring agents, such as, for example, care substances, wetting agents, thickeners, plasticizers, preservatives and perfume oils, and also other customary additives listed below for oxidizing hair coloring agents.
  • further additives customary for hair coloring agents such as, for example, care substances, wetting agents, thickeners, plasticizers, preservatives and perfume oils, and also other customary additives listed below for oxidizing hair coloring agents.
  • the subject of the present invention also includes a hair colorant in which the addition of an oxidizing agent is required.
  • an oxidizing agent is required.
  • the dyes according to the formula (I) given and any known dyes which are absorbed directly onto the hair it also contains additional known oxidation dyes which require oxidative development.
  • oxidation dyes are mainly aromatic p-diamines and p-aminophenols, such as, for example, p-toluenediamine, p-phenylenediamine, p-aminophenol and similar compounds, which are used for the purpose of shading the dyeings with so-called modifiers, such as, for example, Phenylenediamine, resorcinol, m-aminophenol and others can be combined.
  • the dyes of the formula (I) are present in this colorant with the addition of oxidizing agent in a concentration of about 0.01 to 2.0 percent by weight, preferably 0.01 to 1.0 percent by weight.
  • the total content of dyes in this colorant is about 0.1 to 5.0 percent by weight.
  • Oxidation hair colorants are generally alkaline, preferably to pH values of approximately 8.0 to 11.5, the setting being carried out in particular with ammonia. However, other organic amines, for example monoethanolamine or triethanolamine, can also be used for this purpose.
  • the main oxidizing agents used to develop hair color are Hydrogen peroxi d and its addition compounds into consideration.
  • the preparation form of this hair dye can be the same as that of the hair dye without the addition of an oxidizing agent. It is preferably that of a cream or a gel.
  • Common additives in creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, propanol, isopropanol, glycerol or glycols, such as for example ethylene glycol and propylene glycol, or also glycol ethers, and also wetting agents or emulsifiers from the classes of the anionic , cationic, amphoteric or nonionogenic surface-active substances, such as FettalkoholsuIfate, FettaIkoholethersuIfate, alkylsulfonates, AlkyIbenzolsuIfate, AlkyItrimethylammoniumsalze, AlkyIbetaine, ethoxylated fatty alcohols, ethoxylated NonyIphenole, fatty acid alkanolamides, ethoxylated fatty acid ester, also thickeners such as higher fatty alcohols, bentonite, starch, polyacrylic acid
  • ingredients mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, while the thickeners in an amount of about 0.1 to 25 percent by weight and the care substances in an amount of about 0.1 to 5 percent by weight can be contained in the preparations.
  • the use of the preparations mentioned, in which the addition of an oxidizing agent is required, is carried out in a known manner by the hair dye before the treatment with the oxidizing agent mixed and a sufficient amount of the mixture, generally about 50 to 150 ml, is applied to the hair for coloring the hair.
  • a sufficient amount of the mixture generally about 50 to 150 ml, is applied to the hair for coloring the hair.
  • the hair is rinsed with water, optionally subsequently with the aqueous solution of a weak organic acid, such as, for example, citric acid or tartaric acid, and then dried.
  • a weak organic acid such as, for example, citric acid or tartaric acid
  • the hair colorants according to the invention offer, depending on the type and composition of the color components, a wide range of different color shades, ranging from natural shades to highly fashionable, bright shades.
  • the colorants are used either in conjunction with hydrogen peroxide or without an oxidizing agent.
  • the present invention further relates to new 2,6-dinitro-aniline derivatives of the general formula (II)
  • R 1 is C 2 -C 4 -monohydroxyalkyl or C 3 -C 4 -dihydroxyalkyl and Y is one of the radicals C 2 -C 4 -alkyl, C 2 -C 4 -monohydroxyalkyl, C 1 -C 4 -perfluoroalkyl,
  • Monohydroxyalkyl means.
  • the new compounds of the formula (II) are prepared by nucleophilic exchange of an alkoxy group or a halogen atom (A) in the corresponding compound (III) substituted by Y in accordance with the reaction equation below.
  • the preparation of the 2-nitro-aniline derivatives of the formulas (I) and (II) is also possible by dinitration of the aniline derivatives optionally protected, for example by a para-toluenesulfonyl radical, substituted in the para position with X or Y.
  • the 4-chloro or 4-bromo-2,6-dinitro-aniline derivatives can be obtained by chlorination or bromination of the 2,6-dinitro-aniline.
  • the respective unsubstituted amino compounds can be converted to the N-alkyl compounds by the customary alkylation processes.
  • Example 1 2,6-Dinitro-4-trifluoromethyl- (2 ', 3'-dihydroxypropyl) aniline.
  • Bleached natural hair is treated for 20 minutes at room temperature with the solution according to Example 5, then rinsed with water and then dried. The hair is colored bright orange.
  • 50 g of the above hair dye are mixed with 50 ml of hydrogen peroxide solution (6 percent) shortly before use.
  • the mixture is applied to gray human hair and left for 30 minutes at a temperature of 40 degrees Celsius. After rinsing the hair with water and then drying it, it took on a fashionable, reddish blond tone.
  • 50 g of the above hair dye are applied to white human hair and rinsed with water after an exposure time of 20 minutes. The hair is then dried. It is colored in a natural, brown shade.
  • Example 10 Liquid hair dye
  • the above colorant is allowed to act on bleached natural hair at 40 degrees Celsius for 30 minutes. After rinsing the hair with water and then drying it, the hair is colored in a fashionable blonde tone.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Coloring (AREA)

Abstract

On utilise comme colorant dans des produits de teinture pour cheveux un dérivé de 2,6-dinitro-aniline ayant la formule générale (I), dans laquelle R représente H, C1-C4-alkyle, C2-C4 monohydroxyalkyle ou C3-C4-dihydroxyalkyle, et X représente un des résidus C1-C4-alkyle, C2-C4-monohydroxyalkyle, C1-C4-perfluoralkyle, C1-C4-alkoxy, C2-C4-monohydroxyalkoxy, C3-C4-dihydroxyalkoxy ou halogène. Une teinture pour cheveux contient au moins un composé ayant la formule (I) et de nouveaux dérivés de 2,6-dinitro-aniline. Les colorants ayant la formule (I) ont de bonnes propriétés physiologiques et permettent d'obtenir tous les tons de jaune requis pour la teinture, depuis un jaune citron avec une touche de bleu jusqu'à un rouge orangé, en passsant par du pur jaune.
PCT/EP1988/000260 1987-05-04 1988-03-29 Utilisation de derives de 2,6-dinitro-aniline dans des teintures pour cheveux et nouveaux derives de 2,6-dinitro-aniline WO1988008696A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BR888807040A BR8807040A (pt) 1987-05-04 1988-03-29 Aplicacao de um derivado de 2,6-dinitro-anilina,composicao para o tingimento de cabelos e derivados de 2,6-dinitro-anilina
DK716588A DK716588A (da) 1987-05-04 1988-12-22 Anvendelse af 2,6-dinitroanilinderivater i haarfarvemidler
FI890005A FI890005A (fi) 1987-05-04 1989-01-02 Anvaendning av 2,6-dinitro-anilinderivat i haorfaerger och nya 2,6-dinitro-anilinderivat.
NO89890020A NO890020L (no) 1987-05-04 1989-01-03 Anvendelse av 2,6-dinitroanilinderivater i haarfarvemidlerog nye 2,6-dinitroanilinderivater.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3714775.7 1987-05-04
DE19873714775 DE3714775A1 (de) 1987-05-04 1987-05-04 Verwendung von 2,6-dinitro-anilinderivaten in haarfaerbemitteln und neue 2,6-dinitro-anilinderivate

Publications (1)

Publication Number Publication Date
WO1988008696A1 true WO1988008696A1 (fr) 1988-11-17

Family

ID=6326787

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1988/000260 WO1988008696A1 (fr) 1987-05-04 1988-03-29 Utilisation de derives de 2,6-dinitro-aniline dans des teintures pour cheveux et nouveaux derives de 2,6-dinitro-aniline

Country Status (11)

Country Link
US (1) US5030241A (fr)
EP (1) EP0289782B1 (fr)
JP (1) JP2539262B2 (fr)
AT (1) ATE72967T1 (fr)
AU (1) AU605280B2 (fr)
BR (1) BR8807040A (fr)
DE (2) DE3714775A1 (fr)
ES (1) ES2033970T3 (fr)
FI (1) FI890005A (fr)
GR (2) GR880300189T1 (fr)
WO (1) WO1988008696A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3917114C3 (de) * 1989-05-26 1996-08-14 Schwarzkopf Gmbh Hans Neue Nitro-p-phenylendiaminderivate, Verfahren zu ihrer Herstellung sowie Färbemittel für keratinische Fasern, die diese enthalten
US5961664A (en) * 1997-07-10 1999-10-05 Bristol-Myers Squibb Company Direct hair dye compositions and methods containing novel anthraquinone mixtures
DE102015218077A1 (de) * 2015-09-21 2017-03-23 Henkel Ag & Co. Kgaa Haar schonendes Oxidationsfärbe- oder -blondiermittel und schonendes Haarfärbe- oder -blondierverfahren
RU2749263C2 (ru) * 2015-11-20 2021-06-07 Хенкель Аг Унд Ко. Кгаа Щадящие волосы средства и способ окислительного окрашивания волос или блондирования
DE102016209468A1 (de) * 2016-05-31 2017-11-30 Henkel Ag & Co. Kgaa Haar schonende Mittel und Verfahren zur oxidativen Haarfärbung oder Blondierung mit ausgewählten Dicarbonsäuren

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1511025A (fr) * 1966-12-13 1968-01-26 Daikin Ind Ltd Procédé de préparation de n, n-di(hydroxyalkyl)-2-trifluorométhyl-4,6-dinitroanilines et nouveaux produits ainsi obtenus
GB1116138A (en) * 1965-10-28 1968-06-06 Hoechst Ag Water-soluble basic nitro dyestuffs, their salts and process for their manufacture
US3654363A (en) * 1969-10-09 1972-04-04 Revlon Process of mono- and di-nitrating p-phenylene diamine compounds
US3699167A (en) * 1969-11-17 1972-10-17 Ansal Co The 1-alkyl-4-bis(haloalkyl)amino-3,5-dinitrobenzene
GB2090853A (en) * 1981-01-14 1982-07-21 Oreal Dyeing compositions for keratin fibres, based on 3-nitro- ortho-phenylenediamines, and certain 3-nitro-ortho- phenylenediamines used therein
US4395577A (en) * 1981-10-22 1983-07-26 American Cyanamid Company Preparation of 3-chloromethyl-4-alkyl-nitrobenzene by chloromethylation
GB2168369A (en) * 1984-12-13 1986-06-18 Oreal New 2,4-dinitro anilines useful as hair dyes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE928909C (de) * 1951-02-07 1955-06-13 Kleinol Produktion G M B H Verfahren zum Faerben von tierischen Fasern, insbesondere von menschlichen Haaren, ohne Zuhilfenahme von Oxydationsmitteln
US3488138A (en) * 1962-10-18 1970-01-06 Clairol Inc Stabilized nitro-aminobenzene dyeing compositions
CA1024071A (fr) * 1972-08-09 1978-01-10 George Alperin Teinture semi-permanente pour cheveux contenant un colorant nitro, une amine quaternaire et certaines amides d'acides gras n-oxyacilees
DE3442757A1 (de) * 1984-11-23 1986-05-28 Wella Ag, 6100 Darmstadt Verwendung von 2-nitroanilinderivaten in haarfaerbemitteln und neue 2-nitroanilinderivate
LU86256A1 (fr) * 1986-01-20 1988-01-20 Oreal Procede de teinture des fibres keratiniques avec du 5,6-dihydroxyindole associe avec un iodure

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1116138A (en) * 1965-10-28 1968-06-06 Hoechst Ag Water-soluble basic nitro dyestuffs, their salts and process for their manufacture
FR1511025A (fr) * 1966-12-13 1968-01-26 Daikin Ind Ltd Procédé de préparation de n, n-di(hydroxyalkyl)-2-trifluorométhyl-4,6-dinitroanilines et nouveaux produits ainsi obtenus
US3654363A (en) * 1969-10-09 1972-04-04 Revlon Process of mono- and di-nitrating p-phenylene diamine compounds
US3699167A (en) * 1969-11-17 1972-10-17 Ansal Co The 1-alkyl-4-bis(haloalkyl)amino-3,5-dinitrobenzene
GB2090853A (en) * 1981-01-14 1982-07-21 Oreal Dyeing compositions for keratin fibres, based on 3-nitro- ortho-phenylenediamines, and certain 3-nitro-ortho- phenylenediamines used therein
US4395577A (en) * 1981-10-22 1983-07-26 American Cyanamid Company Preparation of 3-chloromethyl-4-alkyl-nitrobenzene by chloromethylation
GB2168369A (en) * 1984-12-13 1986-06-18 Oreal New 2,4-dinitro anilines useful as hair dyes

Also Published As

Publication number Publication date
FI890005A0 (fi) 1989-01-02
JPH01503240A (ja) 1989-11-02
GR880300189T1 (en) 1989-02-23
GR3004802T3 (fr) 1993-04-28
AU605280B2 (en) 1991-01-10
AU1494688A (en) 1988-12-06
EP0289782B1 (fr) 1992-03-04
DE3868684D1 (de) 1992-04-09
US5030241A (en) 1991-07-09
FI890005A (fi) 1989-01-02
ES2033970T3 (es) 1993-04-01
BR8807040A (pt) 1989-10-31
DE3714775A1 (de) 1988-11-24
EP0289782A1 (fr) 1988-11-09
ATE72967T1 (de) 1992-03-15
JP2539262B2 (ja) 1996-10-02

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